Nike Air Flight One — Michael Jordan 

The Air Flight One isn't a bad shoe by any means, it actually is underrated in terms of style, performance, and comfort—which may be why Mike took a break from the XIs to rock them for a home game during the Bulls '95 playoff series against the Magic. A nod to his respect for Penny? A dig at a young rival? Maybe. Either way it was odd seeing MJ rock anything other than a pair of Jordans on the court. If Tinker gave up on the Jordan line like he was advised to do, we might have seen Mike rocking Penny's for a minute longer.